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Top Holiday Rentals in Oakham

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (16)
"Our stay at this property was great. Very clean and spacious. Area was very accessible to main roads. Our hosts were very responsive from booking through to the end of our stay. Will look to stay next time we visit Worcester "
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Dove Cabin up in the Trees

10.0 out of 10, Exceptional, (18)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is £196
includes taxes & fees
11 Aug - 12 Aug
Dove Cabin up in the Trees

Serene 1-bedroom suite on 65 acre horse property

10.0 out of 10, Exceptional, (20)
"Had such a wonderful stay at this space. Brent was very communicative about the check in/check out process which was greatly appreciated. The main living room area is very spacious and the bedroom was comfortable. I would definitely stay here again in the future!"
The price is £174
includes taxes & fees
13 Aug - 14 Aug
Serene 1-bedroom suite on 65 acre horse property

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (9)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (1)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is £387
includes taxes & fees
11 Aug - 12 Aug
Spacious 4-bedroom with four and half bathrooms

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (20)
"Matressess were outdated but otherwise great!"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (173)
"Beautiful house and grounds! Very private with lots of room along with homey touches. Kids loved the toy cabinet and the pool table. Easy access to Boston. We thoroughly enjoyed our Easter weekend there! "
Beautiful Lakefront Home with Private Beach

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

10.0 out of 10, Exceptional, (1)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (16)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (16)
"You will hear a little road noice but other then that it was perfect! Extremely clean and a great location. Highly recommend "
3 Bed / 1.5 Bath Townhome

Beautiful two-story home close to downtown worcester 5beds-4bedroom

9.0 out of 10, Wonderful, (13)
"Nice place."
The price is £315
includes taxes & fees
21 Aug - 22 Aug
Beautiful two-story home close to downtown worcester 5beds-4bedroom

New renovation cozy house in Worcester

9.8 out of 10, Exceptional, (11)
"This was a great spot for myself and my coaches when we had to travel to the area for a cheerleading competition."
New renovation cozy house in Worcester

Charming 3-bedroom apartment in historic Grafton with WiFi

10.0 out of 10, Exceptional, (11)
"We appreciated the communication and space we had! Neighborhood was quiet and host gave amazing recommendations. "
Charming 3-bedroom apartment in historic Grafton with WiFi

Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

9.0 out of 10, Wonderful, (2)
"House was new, bright, and clean. "
Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (190)
"This was our third time staying, and definately won’t be our last!"
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

10.0 out of 10, Exceptional, (20)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
The price is £417
includes taxes & fees
26 Aug - 27 Aug
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (28)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
Luxury Home, Pool, fireplace

Leicester Lake Front Home, Come Relax!

10.0 out of 10, Exceptional, (26)
"Great family time and comfortable house to spend time with family during a visit to see our daughter at Holy Cross! "
Leicester Lake Front Home, Come Relax!

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

9.8 out of 10, Exceptional, (10)
"Property is in excellent condition and well appointed. We enjoyed our stay."
The price is £456
includes taxes & fees
9 Sept - 10 Sept
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Home Away from Home!

9.2 out of 10, Wonderful, (11)
"Lots of bedrooms with a great family gathering space. Quiet neighborhood. Would stay again at this property. Nicely decorated. "
The price is £299
includes taxes & fees
11 Aug - 12 Aug
Home Away from Home!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakham Hotel Reviews

Frequently asked questions

Are there holiday rentals in Oakham?

Yes, there are holiday rentals close to the most popular sights in Oakham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakham has to offer?

Spacious 4-bedroom with four and half bathrooms: This holiday home rental outside of Oakham is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as Green Hill Park, or get out into nature at a spot like Rock House Reservation. In the wider area, you’ll find Hardwick Vineyard and Winery and Wachusett Mountain State Reservation.

What’s a holiday rental in Oakham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakham. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.